15644-90-3

Usage

Uses

Used in Pharmaceutical Industry:
6-Methoxy-2-methylquinolin-4-ol is used as a bioactive compound for its potential antibacterial and antifungal properties, which can contribute to the development of new drugs to combat resistant infections.
Used in Agrochemical Industry:
In the agrochemical sector, 6-Methoxy-2-methylquinolin-4-ol is utilized as a bioactive ingredient for its potential to control or prevent bacterial and fungal infections in crops, thereby enhancing agricultural productivity and crop protection.
Further research is necessary to fully understand the scope of applications and benefits of 6-methoxy-2-methylquinolin-4-ol in these industries and to develop effective formulations and delivery systems for its practical use.

InChI:InChI=1/C11H11NO2/c1-7-5-11(13)9-6-8(14-2)3-4-10(9)12-7/h3-6H,1-2H3,(H,12,13)

Upstream product

• 80056-93-5 ethyl 3-[(4-methoxyphenyl)imino]butanoate 
• 50593-73-2 4-chloro-6-methoxy-2-methylquinoline 
• 104-94-9 4-methoxy-aniline 
• 500584-76-9 (4-hydroxy-6-methoxy-[2]quinolyl)-acetic acid ethyl ester 
• 141-97-9 ethyl acetoacetate 
• 33240-23-2 ethyl 3-((4-methoxyphenyl)amino)but-2-enoate 
• 33240-23-2 ethyl (Z)-3-(4-methoxyanilino)-2-butenoate 

Downstream Products

• 110150-61-3 2-(2,3-dimethoxy-trans-styryl)-6-methoxy-quinolin-4-ol 
• 28102-96-7 2-methyl-4-mercapto-6-methoxyquinoline 
• 856095-00-6 4-bromo-6-methoxy-2-methylquinoline 
• 74767-30-9 4-{[1-(4-Hydroxy-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid 6-methoxy-2-methyl-quinolin-4-yl ester 
• 74767-27-4 4-{[1-(4-Acetylamino-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid 6-chloro-2-methyl-quinolin-4-yl ester 
• 74767-28-5 4-{[1-(4-Acetylamino-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid 6-methoxy-2-methyl-quinolin-4-yl ester 
• 74767-24-1 4-{[1-(4-Chloro-phenyl)-meth-(E)-ylidene]-amino}-benzoic acid 6-methoxy-2-methyl-quinolin-4-yl ester 
• 74767-10-5 2-{[1-(4-Hydroxy-phenyl)-meth-(Z)-ylidene]-amino}-benzoic acid 6-methoxy-2-methyl-quinolin-4-yl ester 
• 74767-07-0 2-{[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-amino}-benzoic acid 6-methoxy-2-methyl-quinolin-4-yl ester 
• 74767-17-2 2-{[1-(4-Dimethylamino-phenyl)-meth-(Z)-ylidene]-amino}-benzoic acid 6-methoxy-2-methyl-quinolin-4-yl ester 
• 74767-14-9 2-{[1-(4-Acetylamino-phenyl)-meth-(Z)-ylidene]-amino}-benzoic acid 6-methoxy-2-methyl-quinolin-4-yl ester 
• 50593-73-2 4-chloro-6-methoxy-2-methylquinoline 
• 108273-35-4 (6-methoxy-2-methyl-[4]quinolylmercapto)-acetic acid 
• 101875-73-4 4-Chlor-6-methoxy-2-<4-nitro-styryl>-chinolin 

Relevant academic research and scientific papers

Synthesis and antibacterial activities of some quinoline substituted quinoxaline derivatives

p-Anisidine (1) on treatment with ethyl acetoacetate gave 1-(ethyl-3-[(4-methoxyphenyl)imino]butanoate) (2), which on cyclization in hot Dowtherm oil gave 4-hydroxy-6-methoxy-2-methylquinoline (3). The latter, on chlorination with SO2Cl2/

Design, synthesis, and antitumor evaluation of quinoline-imidazole derivatives

A series of compounds bearing quinoline-imidazole (8a–e, 9a–e, 10a–e, 11a–e, and 12a–e) not reported previously were designed and synthesized. The target compounds were evaluated for antitumor activity against A549, PC-3, HepG2, and MCF-7 cells by the MTT method, with NVP-BEZ235 being the positive control. Most compounds showed moderate activity and compound 12a showed the best activity against HepG2, A549, and PC-3 cells, with half-maximal inhibitory concentration (IC50) values of 2.42 ± 1.02 μM, 6.29 ± 0.99 μM, and 5.11 ± 1.00 μM, respectively, which was equal to NVP-BEZ235 (0.54 ± 0.13 μM, 0.36 ± 0.06 μM, 0.20 ± 0.01 μM). Besides, the IC50 value of 12a against the cell line WI-38 (human fetal lung fibroblasts) was 32.8 ± 1.23 μM, indicating that the target compounds were selective for cancer cells. So, 11a and 12a were evaluated against PI3Kα and mTOR to find out if the compounds acted through the PI3K-Akt-mTOR signal transduction pathway. The inhibition ratios to PI3Kα and mTOR were slightly lower than that of NVP-BEZ235, suggesting there may be some other mechanisms of action. The structure–activity relationships and docking study of 11a and 12a revealed that the latter was superior. Moreover, the target compounds showed better in vitro anticancer activity when the C-6 of the quinoline ring was replaced by a bromine atom.

Design, synthesis, and biological evaluation of new quinoline-based heterocyclic derivatives as novel antibacterial agents

A novel series of quinolone-based heterocyclic derivatives including thiadiazine, thiadiazoles, and triazole were synthesized and their in vitro antibacterial activity against Gram-positive and Gram-negative bacteria were evaluated. Newly synthesized deri

Design, synthesis, and evaluation of new 2-(quinoline-4-yloxy)acetamide-based antituberculosis agents

Using a classical molecular simplification approach, a series of 36 quinolines were synthesized and evaluated as in vitro inhibitors of Mycobacterium tuberculosis (M. tuberculosis) growth. Structure–activity relationship (SAR) studies leaded to potent antitubercular agents, with minimum inhibitory concentration (MIC) values as low as 0.3 μM against M. tuberculosis H37Rv reference strain. Furthermore, the lead compounds were active against multidrug-resistant strains, without cross-resistance with some first- and second-line drugs. Testing the molecules against a spontaneous mutant strain containing a single mutation in the qcrB gene (T313A) indicated that the synthesized quinolines targeted the cytochrome bc1 complex. In addition, leading compounds were devoid of apparent toxicity to HepG2 and Vero cells and showed moderate elimination rates in human liver S9 fractions. Finally, the selected structures inhibited M. tuberculosis growth in a macrophage model of tuberculosis infection. Taken together, these data indicate that this class of compounds may furnish candidates for the future development of antituberculosis drugs.

ANTIMALARIAL COMPOUNDS

Antimalarial compounds of the formula: in which n is 1 or 2; X is C or N; R1 is a moiety comprising a secondary amine and a tertiary amine joined by a C2 to C4 alkyl chain; and R2 is CF3, F, or H, or an analog, combination, derivative, prodrug, stereoisomer, or pharmaceutically acceptable salt thereof. Pharmaceutical compounds including the antimalarial compounds. Methods of treating or preventing malaria comprising administering an effective amount of the antimalarial compounds.

Synthesis, Structure-Activity Relationship, and Antimalarial Efficacy of 6-Chloro-2-arylvinylquinolines

There is an urgent need to develop new efficacious antimalarials to address the emerging drug-resistant clinical cases. Our previous phenotypic screening identified styrylquinoline UCF501 as a promising antimalarial compound. To optimize UCF501, we herein report a detailed structure-activity relationship study of 2-arylvinylquinolines, leading to the discovery of potent, low nanomolar antiplasmodial compounds against a Plasmodium falciparum CQ-resistant Dd2 strain, with excellent selectivity profiles (resistance index 200). Several metabolically stable 2-arylvinylquinolines are identified as fast-acting agents that kill asexual blood-stage parasites at the trophozoite phase, and the most promising compound 24 also demonstrates transmission blocking potential. Additionally, the monophosphate salt of 24 exhibits excellent in vivo antimalarial efficacy in the murine model without noticeable toxicity. Thus, the 2-arylvinylquinolines represent a promising class of antimalarial drug leads.

Syntheses and evaluation of new Quinoline derivatives for inhibition of hnRNP K in regulating oncogene c-myc transcription

Aberrant overexpression of heterogeneous nuclear ribonucleoprotein K (hnRNP K) is a key feature in oncogenesis and progression of many human cancers. hnRNP K has been found to be a transcriptional activator to up-regulate c-myc gene transcription, a critical proto-oncogene for regulation of cell growth and differentiation. Therefore, down-regulation of c-myc transcription by inhibiting hnRNP K through disrupting its binding to c-myc gene promoter is a potential approach for cancer therapy. In the present study, we synthesized and screened a series of Quinoline derivatives and evaluated their binding affinity for hnRNP K. Among these derivatives, (E)-1-(4-methoxyphenyl)-3-(4-morpholino-6-nitroquinolin-2-yl)prop-2-en-1-one (compound 25) was determined to be the first-reported hnRNP K binding ligand with its KD values of 4.6 and 2.6 μM measured with SPR and MST, respectively. Subsequent evaluation showed that the binding of compound 25 to hnRNP K could disrupt its unfolding of c-myc promoter i-motif, resulting in down-regulation of c-myc transcription. Compound 25 showed a selective anti-proliferative effect on human cancer cell lines with IC50 values ranged from 1.36 to 3.59 μM. Compound 25 exhibited good tumor growth inhibition in a Hela xenograft tumor model, which might be related to its binding with hnRNP K. These findings illustrated that inhibition of DNA-binding protein hnRNP K by compound 25 could be a new and selective strategy of regulating oncogene transcription instead of targeting promoter DNA secondary structures such as G-quadruplexes or i-motifs.

Synthesis and identification of quinoline derivatives as topoisomerase I inhibitors with potent antipsoriasis activity in an animal model

Psoriasis is a chronic inflammatory and immune-mediated skin disease. Although certain agents have shown clinical success in treating psoriasis, development of safe and effective strategies for the treatment of this condition remains important. Research suggests that DNA topoisomerase I (Topo I)inhibitors may have potent psoriasis-ameliorating effects. Here, 25 quinoline derivatives were synthesized and identified as Topo I inhibitors. These compounds inhibited the 12–O–tetradecanoylphorbol-13-acetate-induced mouse ear inflammation. The most potent analogs, 5i and 5l, suppressed the expression of inflammatory cytokines in lipopolysaccharide-stimulated HaCaT cells. Additionally, the lead compounds significantly improved imiquimod-induced psoriasis-like inflammation in mice. Moreover, the expression levels of cytokines and inflammatory mediators, such as interleukin (IL)-17A, IL-22, IL-23, nuclear factor-κB subunit p65, tumor necrosis factor-α, and interferon-γ, were dramatically inhibited in the dorsal skin of 5i- and 5l-treated mice. These findings indicate that the inhibition of Topo I activity may potentially be an effective strategy for psoriasis treatment.

Design, Synthesis, and Antifungal Evaluation of Novel Quinoline Derivatives Inspired from Natural Quinine Alkaloids

Inspired by quinine and its analogues, we designed, synthesized, and evaluated two series of quinoline small molecular compounds (a and 2a) and six series of quinoline derivatives (3a-f) for their antifungal activities. The results showed that compounds 3e and 3f series exhibited significant fungicidal activities. Significantly, compounds 3f-4 (EC50 = 0.41 μg/mL) and 3f-28 (EC50 = 0.55 μg/mL) displayed the superior in vitro fungicidal activity and the potent in vivo curative effect against Sclerotinia sclerotiorum. Preliminary mechanism studies showed that compounds 3f-4 and 3f-28 could cause changes in the cell membrane permeability, accumulation of reactive oxygen species, loss of mitochondrial membrane potential, and effective inhibition of germination and formation of S. sclerotiorum sclerotia. These results indicate that compounds 3f-4 and 3f-28 are novel potential fungicidal candidates against S. sclerotiorum derived from natural products.

Discovery of potent 4-aminoquinoline hydrazone inhibitors of NRH:quinoneoxidoreductase-2 (NQO2)

(NRH):quinone oxidoreductase 2 (NQO2) is associated with various processes involved in cancer initiation and progression probably via the production of ROS during quinone metabolism. Thus, there is a need to develop inhibitors of NQO2 that are active in v